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Synthesis 2012(7): 1026-1029  
DOI: 10.1055/s-0031-1289710
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Preparation of Halo-1,3-thiazoles: Important Building Blocks for Materials and Pharmaceutical Synthesis

Alan M. Grubb, Michael J. Schmidt, Alexander J. Seed, Paul Sampson*
Department of Chemistry and Biochemistry, Kent State University, Kent, OH 44242-0001, USA
e-Mail: psampson@kent.edu;
Further Information

Publication History

Received 3 November 2011
Publication Date:
16 February 2012 (online)

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Abstract

Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed.

Key words

halogenation - bromine - iodine - 1,3-thiazole - heterocycles

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16

2-Amino-5-bromo-1,3-thiazole is commercially available ($3509/mol from Accela ChemBio, Inc.)

26

POBr3 is commercially available ($766/mol from Alfa Aesar).